


The Tik Tok™ Love a Trans Woman Challenge

by Rhonda



Series: The Career Boy Cinematic Universe [2]
Category: Kuroshitsuji | Black Butler
Genre: Alternate Universe - American, Alternate Universe - Modern Setting, Anal Sex, Closet Sex, Clothed Sex, Coming Out, Deepthroating, Enthusiastic Consent, F/M, Female Pronouns for Grell Sutcliff, Fluff and Smut, Friends With Benefits, Friends to Friends With Benefits to Lovers, Friends to Lovers, Gender Dysphoria, Happy Sex, Office Sex, Open Relationships, Oral Sex, Pining, Porn With Plot, Porn with Feelings, Semi-Public Sex, Smut, Trans Character, Trans Female Character
Language: English
Status: Completed
Published: 2020-07-11
Updated: 2020-07-11
Packaged: 2021-03-05 05:34:08
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 8,166
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25199329
Author URL: https://archiveofourown.org/users/Rhonda/pseuds/Rhonda
Summary: Ronald has been crushing on his redheaded coworker for as long as he's known her. One day, things between them escalate and he's left trying to figure out how to escalate them further.All the while, unbeknownst to him, she's been a bit closer with their boss than he'd want it to seem.
Relationships: Background William T. Spears/Grell Sutcliff, Ronald Knox/Grell Sutcliff
Series: The Career Boy Cinematic Universe [2]
Series URL: https://archiveofourown.org/series/1824865
Comments: 2
Kudos: 13





	The Tik Tok™ Love a Trans Woman Challenge

It had all started one day in the break room. Ronald Knox had gone in to text that cute girl in Accounting. He hated texting at his cubicle, he could always feel William’s eyes burning a hole in the back of his neck every time he goofed off at his desk and it felt like the break room was the only safe haven from the towering panopticon that was their office floor. Grelle had been snacking on some of the communal fruits. She picked up a banana, giggled to herself and looked around for someone to do a bit at. Ron was the only person in the break room at the time and Grelle sauntered over to him plopping her butt down on the table next to where Ron was texting. He looked up at her, and she looked down at him with a shark faced grin. For a moment they sat in silence and right before Ron was about to ask what she needed she spoke up.

“Hey, wanna watch me eat this banana in two bites?” She said, mirth barely contained on her face as she peeled it.

“Sure, okay,” Ronald said, not really sure where she was going with it. With a twinkle in her eyes Grelle gently slid a tooth a quarter inch down the surface of the banana.

“That’s bite number one~”

* * *

Ronald had only been with the company for a year but he already knew what the best broom closets were, and Grelle giggled as he led her down hallway after hallway and up a few flights of stairs. It wasn’t the closest one but it was the most luxurious being quite spacious, seldom used, uniquely free of the smell of clorox, and most importantly it had a pile of plastic bags full of clean towels that were cozy enough to roll around on with a girl if things got that far. He looked back at Grelle. She was grinning at him like a schoolgirl and the thought of fooling around with her was making him nervous about someone seeing the bulge in his pants. Luckily the hallways here were mostly cleared out.

Ronald had been crushing hard on the businesswoman since the day he was hired but it seemed like she was always trying to get into their boss William’s pants. He didn’t think she had much of a chance, and maybe she had finally realized that. The dude was married and had kids, besides he was so professional he seemed like the least likely man to ever experience attraction to anyone. He never came out with the office for drinks nor did he ever see the man pal around with anyone. Dude was practically a robot, he had to have conceived his kids in a lab. On the occasions that Ronald was called into his office like a naughty schoolboy, he noted just how adult and unfun he kept his surroundings. No office doodads or kitten posters or a picture of his family or even any funny cut out newspaper comics. The man didn’t even like Dilbert, the last bastion of humor for even the most jaded of office drones.

Ronald had up until now taken the conciliation of flirting with some of the more mundane office chicks, giving him his intimate knowledge of the best places to pork while on the clock. He’d even taken a few of them on dates, but they never really worked out. He just found so many women so fundamentally unlikeable, that he’d end things even when the other party didn’t realize anything was wrong. Luckily he was charming enough to never get in trouble with HR and the girls that he had spent nights with spread rumors of his prowess in bed. 

The girls were fun but Ronald had wanted a woman, he was just afraid Grelle might be too much woman for him to handle. She was near to a decade his senior. Between her husky voice, long red hair that she never wore up unlike all the other women in the office, her impeccable fashion that always showed a little bit more skin than was technically professional, and her legs that just went on and on for miles, he felt like a little boy fantasizing about the girls in Penthouse Magazine. But for as much as he wanted to bed her, he also deeply wanted to love her. She was so funny, and always made him laugh when she would stop by his desk to chat. He'd never felt so comfortable talking to a woman before. He was good at being charming but that was only skin deep. Grelle disarmed him, when he was with her he felt like he was hanging out with his guy friends. She also had a mean streak and there was something about mean girls that Ronald had always had a thing for. They’d gossip about office drama and she’d say the most down right nasty things about their coworkers. She’d ask him for favors that she’d never repay and he’d never be able to refuse, most of them involving him finishing some work of hers while she left work early. 

Ronald closed the door behind them, locking it to make sure no one stumbled upon them while looking for some extra toilet paper. Luckily the janitorial staff didn’t come in till late at night so there wasn’t much of anyone who could disturb them here. He turned around and looked into those big beautiful eyes of hers. Well, who knows where this might go. He took the initiative and leaned in to give her a kiss only to face plant into her outstretched palm.

“There’s one thing that I need to tell you before we do anything. I’ve learned I need to say this up front or you might hit me. In fact, you have to promise you won’t.”

“What? Grelle you’re my friend. I’d never hit a woman, holy shit.”

“Well yeah about that, um… just promise Ronnie, okay. At the very least not in the face.”

“Yeah, I promise I won’t ever hit you. You’re one of my best friends here and I can’t think of anything that would change that.”

“Well... I’m a trans woman.” She said flinching like saying the words was enough to set off a spark and catch fire to all the shelved chemicals that sat inert around them. 

“I uh, oh.” That was not something he had been expecting. “So have you, like had _the surgery_ or whatever?” He immediately cringed at his words, that was probably shit she got all the time; but, he reasoned, it was relevant to their immediate future.

“Sort of, like, I’ve had my testes removed but I still have a… um... wiener,” she said sheepishly, rubbing the tips of her pointer fingers together. “There isn’t a surgeon on Earth that can give me what I really want...” she said trailing off and looking into the middle distance.

This was a lot to take in so fast. But then, it really wasn’t. It didn’t change anything, Ronald loved whom he loved. He had known _of_ trans people, but he’d never met one before in real life. That he knew of. He had once dated a girl in college who seemingly wouldn’t shut up about the indignanty of ‘trans identified males’ constantly invading women’s spaces despite the fact she had never actually met one either. She was wrong about a lot of stuff and he hoped he hadn’t internalized any of what she had said.

Oh, but Grelle looked so vulnerable and cute right now and if he already had feelings for her he had even more now. All he wanted to do was kiss her. He leaned in and this time she didn’t rebuff him. Quite the opposite she pulled him into her like he was water and she was lost in the desert. Her lips were soft and full and sweet and the entire world to him.

He embraced her and she him. He ran his hands along the length of her body feeling the soft curves of her hips all the way up to her smooth shoulders. She was taller than him with the added height that her heels gave her, but not by so much, and here in the darkness revealing herself to him she felt small and delicate.

He backed her up against the wall, and she needily pressed her hips into his while he trailed his hand up to grip at a small breast through her blouse. They were cute, and they fit her perfectly, just another thing that separated her from the office bunnies he had been chasing. They were no substitute for the real thing. He pressed his face into her chest as she arched her back and ran a hand through his hair and over the back of his head.

He pressed his leg up between her bumping at her crotch. Logically he had realized she had a penis, but it wasn’t until he felt her bulge pressing up against his leg that he really processed the reality of it. There was something about it that was hotter than he’d ever imagined it could be. He pressed into her harder, rolling his thigh against her groin which produced a low needy moan out of her, rolling her hips back in response.

He sunk to his knees before her and rolled up her skirt to see the soft little thing popping out from between her legs beneath her roughly textured cottony white panties. He ran the material between his fingers, surely she could afford something softer.

“Cotton holds the tuck better,” she breathed, reading his expression, “You don’t have to use your mouth on me if you’re not ready, I won’t be offended I promise.” But he really wanted to, he’d wanted to since he first saw the woman, but now seeing her cute little penis twitching he needed it in a way he didn’t realize he desperately had all his life until now.

Without much fanfare he yanked her panties down her to her thighs. She eeped and quickly pressed her legs together while her cock (hen?) sprung up at attention. He looked up at her to see if the move was just reflexive or was indicative of any reservations. He couldn’t see too well in the dim light but her face was bashful as she nodded and mewled a soft plea for him to continue.

He didn’t really know how to start. He wasn’t sure if he was supposed to treat her like she was a cis (that was the right term right?) woman or go down on her like he was sucking a cock. Neither really seemed appropriate. He probingly pressed his face into her hen, sliding it along his cheek. She shuddered and gasped at the texture of it rubbing along his stubble. It was the softest thing he had ever felt in his life. It felt like a hundred newly born kittens. It felt like the finest of imported silk ties had been suspended in fabric softener for millenia. It felt like if moonlight had been spun into a quilt and that quilt was a precious family heirloom that had been sitting in the attic since he was a boy, only for him to discover it one night when it was freezing cold during a harsh winter storm and all the bedding had been left wet in the washing machine which had stopped mid cycle when the power went cut out; wrapping it around himself while he sat next to the smoldering fireplace and dreamed about how soft a girl’s hen could possibly be. It was so soft.

The foreskin around it was too big for it, and it bunched up and pulled back and forth as he nuzzled it. He took the base between his lips and sucked. She gently rolled her hips and he slid his arms up her legs, starting at the toes of her three inch heels, trailing up over her ankles and calves still covered by white kneesocks, over the bundled up panties now wrapped around her knees, sliding up her thighs and up up up to grip softly at her butt. It was full and soft and cold. He endeavored to warm it up with his hands.

Meanwhile he pressed little kisses around her cleanly shaven base before pulling back to appraise the tip. He took off his glasses and put them in his pocket so he could get a better look at the thing up close. It was so cute, oversized foreskin bunched up like someone eating a super sour candy for the first time. He giggled and Grelle seized up a little, clearly sensitive to being laughed at in this situation. Usually, no one laughed harder at her ridiculous pratfalls than her but here and now she seemed very defensive of her body.

“You’re just so cute is all,” he said and the tension in her frame left as quickly as it arrived. She pet her hands through his hair affirmingly and he smiled up at her just for her to blush and look away shyly. This Grelle was nothing like the Grelle he had grown to befriend and pine for over the last year. Not that he wasn’t head over heels for this Grelle too, it was simply a side he never expected her to have. In all of his private fantasies she had always been dominant in bed, but here and now with her she was just so bashful and pliant. He had no complaints though.

He took the end of her hen into his mouth, gently working at it with his lips, and she let out gasp at the return of his mouth and threw her head back. He pushed the tip of his tongue underneath her foreskin and circled it around falling in love with the smooth texture of her hen’s head. He loved how it felt in his mouth so he just kept swirling his tongue and sucking at it as her voice got louder above him. She called out his name in little mewls that got faster as he ran his hands up and down the front of her thighs, eventually reaching up to pet at the soft skin between her legs.

“C- c- cumming!” she whispered into the room as his only warning. She shuddered violently and a very small amount of clear sticky goop dribbled out of her and onto his tongue. It wasn’t at all like the torrent of white hot jizz that he had been steeling himself for. He was a touch disappointed actually, but what he got was adorable and sexy in its own right. Even her cum was cute and girly. She wrapped her arms around him when he stood up and kissed her. She was so warm and her skin was flushed and slick with sweat. She looked into his eyes with an expression that told him she was ready to return the favor.

Just then both of their phones buzzed. He pulled his out of his pants pocket and was temporarily blinded by the light of its screen.

“Shit we have an emergency meeting. Marketing can’t decide whether the next magazine ad should be azure or cyan and they want all our input,” Ronald said, disappointed that their session would have to be cut short.

“Ugh… fine,” Grelle whined, passionately running her hands down his front before stepping away to pull up her panties. Ronald looked at her. They had made out and he’d even performed oral on her, did this mean they were a thing? No, of course a woman like Grelle would have casual sex, it probably didn’t mean anything to her. But, she must at the very least be attracted to him to do something like this, maybe this was his chance. If he let her walk out that door without confessing his feelings then they would never be able to be more than just friends. Friends with benefits.

“Hey so, uhh... do you maybe wanna, hang out sometime?” He asked as they got cleaned up, Grelle reaching down to put her tuck back in and trying to unwrinkle her pencil skirt. He had intended to sound cool and casual but his voice cracked and he felt like he had come across as needy.

“What, you mean, like, as a date?” she asked, voice unreadable.

“No ha, of course not, it’s just like why don’t we, I don’t know, hang out outside of work. As, like, friends,” Ronald said chickening out. Fuck, why did he just say that, why couldn’t he just let her know how he felt? He tried to salvage it by adding: “Like we could go to get coffee together or something,” but he felt like he had just muddled things worse.

“I think I’d like that,” she said with a smile that evolved into a mischievous smirk. “Well we’ll have to see each other again sometime anyway since I didn’t get the chance to show you that trick with the banana again like I wanted to.” Ronald could have eaten her out again right there but if they didn’t pop back into the office soon someone surely might miss them. And he didn’t want Grelle to get into any more trouble with the boss than she already always was.

* * *

They started spending more time together after that. Instead of just being another friendly face that Grelle would stop and chat with, it felt like she had started seeing him as an actual friend and he was loving it. They’d chat by the copier and in the breakroom and by the water cooler. Occasionally being broken up mid conversation by William who had no patience for their dilly dallying. She was just so funny, the funniest woman he’d ever met. Probably the funniest person he’d ever met. He’d always get excited when he heard the click of her heels, a noise that he’d become incredibly good at picking up out of the standard office din, and more often than not those clicks were the sound of her sauntering over to tell him about some rumor that she heard or a bawdy joke she had come up with. Sometimes she’d talk to him about boys she was interested in which always made him squirm, he was afraid he’d give the wrong expression and expose his crush, or worse make her feel like he didn’t love hearing her talk.

They’d have their lunches together, occasionally he’d take her out and treat her to cheeseburgers, her favorite. She really liked twenty dollar ones from pretentious gastro pubs that tasted like turpentine and liquid smoke, while Ronnie would always just order whatever kind of avocado toast with microgreens they had on the menu. He learned he couldn’t just order an artichoke dip or any of his other favorite appetizers because Grelle would greedily help herself to them. She was ravenous, and a very messy eater besides. She’d always spend at least ten minutes in the restroom washing her face and reapplying her makeup and he’d always wait for her. He knew she appreciated it since she’d always say as much. He got the feeling she was used to being ditched.

One day, after a particularly messy number slathered in barbeque sauce, onion rings, and melted queso that she’d only just managed to keep from spilling all down her blouse, she’d spent over thirty whole actual Gregorian minutes in the restroom just making sure her face was more than clean and presentable. He’d waited for her outside the bathroom door holding her purse, drawing a few stares and giggles from some beach going ex frat boy dudes who clearly thought he was some whipped boyfriend. The thought of him being mistaken for her boyfriend at least made it sting less. That, and how she had kissed him on the cheek after she finally got her concealer to properly cover the grey five-o-clock shadow that electrolysis still hadn’t gotten. She had admitted to him she was super self conscious about it, and how it was the primary reason she was late in the early mornings.

It wasn’t until he got off work that he realized the kiss she had given him had left a clear smooch mark on his cheek. Ugh, and he had been in a meeting in front of everyone including William who had once reprimanded him for coming into work in the same wrinkled suit as the last day, smelling like sex after having spent the night at the apartment of a girl in Marketing. Luckily today he either didn’t notice or was too busy to call him out on it.

They’d spend time together after work too. They’d go to the usual post work get-togethers at the usual bars downtown, but even then they’d hang out together. He was sure a few rumors may have been started from them spending so much time together. He knew Grelle didn’t like it when people would talk about her behind her back even with something as benign as this, but the idea that someone might think they were an item made him giddy. Maybe if everyone in the office believed it were true then it might just become the reality.

Other than bars and the occasional movie, she’d invited him over to her apartment. It was outside the city a fair bit. He needed to take BART all the way to the end of the line to a little identity-less bedroom community. She drove to work, apparently she’d had too many terrible experiences with public transportation and instead preferred the safety and comfort of her red Acura sedan. Ronnie, on the other hand, rode the train all the way to the Tri-Valley just to visit her on a Saturday. He took a Lyft the rest of the way and after knocking on her door and standing there for five minutes with no response he decided to text her. She quickly replied that she was sunbathing out by the pool and that she would meet him at the door to let him in just a minute. It was a nice place, perfectly manicured lawn with large trees providing shade from the hot Californian sun. 

He saw her before she was close enough to call out to. He waved nervously, never knowing exactly what to do in situations like this. She was wearing some red prescription Wayfarers and a little pastel polkadot bikini top with a towel around her waist. She held her hand over her eyes and then waved back, phone in hand, until the awkward way she was holding it caused her to drop it to the pavement. She looked over at him and laughed, he laughed back.

She let him into her apartment while she asked how the ride over was. It was long, almost an hour and a half from Richmond but he didn’t want to trouble her with the gory details. He told her it was nice. She was worth it. He laughed at some joke she made when they stepped into the apartment. He didn’t know what he was expecting, she was such a wild person that he had imagined something out of the ordinary for her home. On the ride over he flipped between theorizing that it might either be messy and trashed or stark and unfurnished. Instead what he found was almost peculiar in its incredible normalcy. Every room looked like the cover of a West Elm catalogue. Almost as though everything was arranged by an interior decorator prepping for a magazine photoshoot. Tasteful, modern, color coordinated, stylish, the kind of home that made you happy just being in it. The kind of unachievable tv commercial perfectness that made you think ‘If only I bought this product my life would be like that!’ Only here it was, being lived in by the most beautiful woman in the world.

They hung out for hours until she said she really wanted to show him that trick with the banana again. He was laying in her impossibly soft bed, room brightly lit by the low evening sun shining through the windows and skylights. She had never taken off her bikini during their time hanging out and now he saw the matching polka dot bottoms that accentuated her curves wonderfully. He had reached in to pop her small breasts out of her top when they started fooling around, and now looking down seeing the way she looked tits-out, the gentle curve of her ass rising behind her while she worked away between his legs, he was hard as diamonds.

She had really opened up to him sexually since their first time, she could still be very submissive in bed, which still took a lot of getting used to, but the shyness was gone, clearly an artifact of her insecurities. She kissed at the shaft of his cock and ran the surface of her tongue across the underside of it. The texture was warm, rough, wet, and it felt nice. Her face was cute and her sunglasses were casually sitting on top of her head until she accidentally bumped them with his cock and they fell down to the rest on the tip of her nose. She looked dorky like that and he snickered. She was surprised at first but just giggled pushing them up the bridge of her nose, and continuing to lick her tongue up and down his length. The cold lens of her sunglasses rubbed up against him as she nuzzled into his cock with her whole face. The feel was strange but not unerotic. She pulled back and lowered her shades briefly to wink at him, before pushing them up and leaning back in.

She nibbled a little at the tip and mouthed the words ‘that’s bite number one’ before sinking all the way to his base in one smooth motion. The warm heat of her insides was like sinking into bed after a long hard day of work. She felt incredible just laying there with him inside her like that. He wasn’t too big which was something a lot of his past girlfriends had actually preferred to his surprise having grown up in the culture that he did, but he was still impressed by her talents. He didn’t think he’d last very long having fixated all afternoon on the soft bounce of Grelle’s boobs as she giggled at her own jokes and her bare smooth legs that she crossed and uncrossed to find a comfortable sitting position. She gently bobbed up and down, never sliding more than a few inches up from his base as she rubbed her hands over the inside of his bare thighs. 

Just then her fingers trailed firmly back and forth against his perineum, a feeling that he had never felt before but overwhelmed him with its unique eroticism. He came hard, hips bucking up into her eager face. Grelle dutifully swallowed down his love and he realized he had shrieked like a little girl. He felt his cheeks begin to flush with shame until he saw the accepting and warm look on her face. Right, she was probably the one person he never needed to feel obligated to perform masculinity in front of, another reason he was so haplessly in love with her.

“All men love being touched here, they just don’t know it or are too afraid of being emasculated to ask their cis girlfriends to,” she said after he had come down, gazing at him with half lidded eyes, cuddling up close to him, “All of the pleasure wires are mixed up down there for people with penises. That’s why I’m so good, I know this territory intimately.” She had a smugness in her voice matched with the smugness on her face, clearly this was a point of pride for her. He wondered just what prostate stimulation must feel like if simply being touched down there had been so intense. 

While they lay there she looked up at him and her smile fell. Her expression changed from one of passive contentment to one of focus, as though she was trying to solve some kind of complicated math problem. Ronnie didn’t want to pry into whatever it was, afraid it might be her questioning their relationship. He didn’t feel like anything was wrong with them, but that was what all the girls he’d ever dumped had said when he dumped them. He really wanted to move forward to being more than just friends with benefits but, the thought of sliding backwards and being just friends, or worse, being just benefits was more than he could handle. It was getting late anyway and he used that as an excuse to not miss the last train home.

* * *

She hadn’t texted him since then and while they weren’t attached at the hip and it wasn’t unusual for them to go a few days without texting he was still worried. By Monday he was secretly sure she was going to break things off. What he didn’t anticipate was that William T. Spears would call him in to speak with him.

His office was as dreadfully adult and professional as it always looked. Actually, it kind of reminded him of Grelle’s apartment in a weird way. It looked like it was out of a catalogue, like the unachievable dream life of marketers. As usual William sat behind his desk, busily typing away at his computer, before turning to him and bidding him take a seat. William looked at him and pushed his glasses up the bridge of his nose, a maneuver that weirdly reminded Ronnie of the way Grelle had adjusted her sunglasses before deepthroating him two days ago. Ronnie desperately tried to not think sexy thoughts while he was about to get chewed out by William. He really didn’t want to get distracted in case he had to debate for his job, but more than that he really didn’t want to form any mental pathways in his brain between being berated by a thirty year old man and the feel of a gorgeous woman’s mouth on his cock. 

“How are you Ronald? Are you well?” William asked. That was not at all what he had been expecting.

“I’m feeling pretty good,” Ronnie lied.

“Do you like working here?” he asked and Ronnie nodded, “I mean, do you like working on this floor? Do you think you might be happier somewhere else in the building?”

“I can’t say that I have any issues with working under you, I know we have different work ethics but I always get my work done on time and I’ve never felt any kind of interpersonal conflict with anyone.”

“What about a transfer, you’re not originally from the Bay right? I imagine there’s a lot about the culture here that doesn’t agree with you. We have an opening at our Seattle branch that I think you would slip right into,” William said. Ronnie loved it here and couldn’t think of anywhere on Earth he’d rather be living. As a matter of fact it seemed like the culture of the Bay Area seemed to agree far worse with William than him. He didn’t really understand what he was trying to get at.

“If I’ve done something to offend you, then I’m sorry, but, I like working here, I like working with everyone. I like working with you even if you never come with any of us to the bar on Fridays.”

“Ah,” William said, changing tactics, “Of course, I think that you’re a fine employee, and I appreciate the important social bonds you’ve forged in our office. It's just that, well, I’ve heard a rumor that you might be getting close to a certain woman in our office...”

“And?” Ronnie asked, trying to not sound indignant, “I’ve many female friends in this company. And yes, some of them I’ve had relations with, there isn’t anything in any of our corporate bylaws that says I can’t.” He didn’t want to say Grelle’s name because he didn’t want to lie and say they were dating when they so clearly weren’t but he was also afraid to say they were just friends and jinx them. He was certain he couldn’t say what they really were because that kind of sexual openness with your boss just wasn’t done.

“Well, it’s just that I think perhaps you might be better off getting close to another one of your lady friends,” William said, his face as unreadable as it always was. Ronnie didn’t want to say her name, but if William wouldn’t either then he felt like he had no choice.

“You mean Grelle?” he said, a brief silence falling over the room.

“Listen, Ronald, I’m trying to look out for your best interest here. I, well, I don’t want you getting hurt. I mean, do you even know _what_ she is?”

“What the hell do you mean, _what_ she is?” Ronnie had no idea what this dude’s damage was but it was getting hard for him to keep his cool and he was raising his voice despite his better judgement. “What she is is my friend, and my crush, and an incredible _woman_ , that’s what she is!”

William opened his mouth to reply but then looked over Ronnie’s shoulder at the door to his office. Ronnie turned around to see a shadow being cast over the foggy glass window.

“Come on in,” William called, tired and seemingly resigned to the interruption.

“Apologies, I was never particularly good at eavesdropping,” said Grelle Sutcliff, who sauntered in through the door closing it behind her. Ronald was surprised to see her, but if William was he was hiding it well. “Willy, I’m hurt that you’d start this conversation without me. When I had said we needed to talk I meant all three of us, not just the two of you boys,” she chided. William flinched almost imperceptibly at the nickname, one that Ronnie had never heard Grelle nor anyone else in the office use for him. 

“What’s going on here?” Ronnie asked, confused.

“Well, Ronnie, I have to confess that over the weeks since we had that tryst in the chemical closet I’ve grown to have feelings for you and I think I’d like to take our relationship to the next level,” she said. Ronnie cringed at the admission of their sex in the office looking to see William not reacting with anger or even disapproval but instead a resignation as he rested his cheek on his fist. Then his mind finally caught up with the rest of her sentence. Grelle, the incredibly amazing beautiful funny sweet Grelle, wanted to be more than just friends with benefits with him? He breathed out a sigh of relief that he had been holding in since he fumbled over his words and said that he didn’t mean ‘hang out’ like a date.

“Okay, yeah I would like that too, a whole lot actually,” Ronnie said to his new girlfriend, before turning to face his boss who still sat there soberly, “But what does any of that have to do with him?” He hardly thought that two coworkers needed permission from their boss to start dating, let alone mention their sex life.

“Ronnie, I have a secret,” Grelle started, “Other than the wiener thing!” she interjected when she saw him glance at the front of her skirt. He rubbed at the back of his head and gave a sheepish smile. “William and I are in a platonic sexual relationship,” she said plain as day looking to gauge Ronnie’s reaction, and when he looked confused William spoke up.

“We’ve been intimate since we first met in college over a decade ago. We’re not together, we’re not dating, we’re not in love; although I hope I don’t just speak for myself when I say that I do love Grelle a whole lot,” he said, Grelle nodded and put her hand on his shoulder.

“Of course I love you, Will. You’re my bffsie,” she said before turning back to Ronnie, “This is something that’s really important to the both of us, and we feel like it’s best to have full disclosure to our potential romantic partners, for obvious reasons, but please know that if you still want to start dating, I’ll only have romantic eyes for you. So… yeah.” She finished entreating Ronnie for his opinion.

“I hope that whatever your decision is that you respect our privacy in this matter and don’t go telling the whole office,” William quickly added.

This was weird, but then again, it really wasn’t. Ronnie had taken the whole trans woman thing in stride, he could roll with this as well. He’d probably have more stuff he’d want to discuss about this as the thoughts came to his mind but as for the moment he was still riding high on the euphoria of finding out the woman whom he loved loved him back. Right now all he wanted to do was kiss the hell out of Grelle and maybe take her out to get terrible hipster burgers. 

“Okay, I’m sure I might need a little bit of time to fully process this new information but for the time being I think I’m okay with it,” Ronnie said. In reality he thought he might be a little more than okay with it, the thought of Grelle coupling with William while she was his girlfriend made him feel hot in a way he’d never felt before. It seemed like Grelle was awakening a whole lot in him. But he still had one pressing question. “What was all that ‘stay away from Grelle’ stuff about?”

“The what stuff?” Grelle said, turning to William.

“I… I’m sorry, both of you,” William began full of a kind of earnest remorse that Ronnie had never seen in the man ever before. “I’d be lying if I said there wasn’t a part of me that didn’t want to share you. But more than that I was just…” William trailed off stuffing his face in his hands before continuing, “I just hate the idea of anyone in this office knowing.”

“That’s understandable,” Ronnie said, still in too good of a mood to want to interrogate the man any further.

“Speak for yourself. William, I’m not happy at all with your conduct! As conciliation Ronald and I will be taking the rest of the day off to make love in my apartment!” Grelle said, taking Ronnie’s hand in hers and leading him up and out of the chair he was sitting in, briskly striding towards the door. Ronnie looked back at William to see what he thought of this development.

“Sure,” he sighed.

Ronnie did really have some work he needed to get done but he didn’t complain, it was nothing that he couldn’t get done tomorrow or the next day or the day after that. As they walked through their office holding hands they drew a few stares. Ronnie pointed at Grelle and whispered “That’s my girlfriend,” to them as they passed by. He was a little high on love right now, and he didn’t realize at first that they weren’t heading towards the parking garage. Instead they now found themselves in front of the same supply closet they had first fooled around in. He looked at Grelle quizzically.

“I really want to stick it to him right now, so we’re not even waiting till we’re off company property,” she said. The way Grelle was talking about their boss right now was erotic in its own right. She locked the door behind them and pounced on him before he could let his eyes adjust to the dark of the closet. She kissed him with a passion that wasn’t there the first two times they had been together, or if it was, was boiling under the surface. He gave as good as he got feeling as though he had been holding himself back up until now.

She pulled him down onto the pile of plastic bags stuffed with clean towels. He ran his hand up and down her back and along her sides. Her long red hair fanned out beneath her, gently cascading over the curves of the full bags like rivers flowing down mountains and into valleys. She was so pretty, and she was his now. Maybe her body wasn’t all his but her love was. And her eyes were so full of love for him right now. Love and want and something else.

“Ronnie, I’m impatient, I was wondering if maybe we could just skip to the main course,” Grelle said, pushing him gently off of her. “I already douched before coming here today on the off chance something like this might happen, and I really just want to feel your cock inside me.” She looked up at him biting her lower lip. He couldn’t say no to that face.

“Okay!” he said eagerly, pulling out his wallet to fish for a condom while she squirted some lub onto her fingers that she apparently had kept in her purse. She pulled down her panties and started twirling her legs in the air enticingly while she prepared herself. He found it, but when he pulled it out it had melted and warped from his body heat. He silently cursed the fact that he hadn’t listened to his sex ed teached when she said to never store condoms in a wallet. He turned to her embarrassed.

“Honey, we’ve both swallowed each other’s cum already, I’m sure if either of us have something we’ve both got it by now,” she said. He figured she was right. “Besides, it’s not like there’s any chance of me getting...” her face fell and she trailed off. She looked to the side and her face scrunched up like she was trying to push some thoughts out of her head.

“Grelle, it’s okay, come here,” he said embracing her. He had never been one to comfort girls before, at least earnestly. He was good at offering empty assurances and hollow platitudes but he had never truly loved a woman enough to feel her pain, and that usually left him distant at best and annoyed at worst. Here with Grelle though, he felt it. He felt how deeply her infertility had traumatized her and he completely and totally wanted to help her through those feelings. He shushed her and pet at her head before placing tender kisses to the crook of her neck.

“Oh Ronnie, I’ve really needed you for a very long time,” she whispered into his ear. She dry sobbed a few times, before regaining her composure. She softly pet at his cheek with her hand as she looked up at him with big eyes. “Ronnie, you’re so sweet.”

“That’s the first time I think that’s ever been true,” he said, more to himself than to his girlfriend. She didn’t dispute or try to assuage him like he was worried she would. Instead she just smiled and wiggled underneath him, letting him know she still wanted to make love.

He’d never had anal sex before. He had girlfriends who had offered as part of a birthday present but he’d been far too uncomfortable at the thought of having any kind of sex that his partner wasn’t intrinsically excited about. He’d heard it was not very pleasurable at all and actually seriously uncomfortable or even painful for the woman but looking down and seeing the way Grelle was looking up at him, hungrily rubbing up against his cock through his pants, he was sure that she really wanted him inside her.

She fumbled with his fly in the dark not really having a good angle from her position amongst the towels, and he eventually pitied her enough to unzip it himself. He popped himself out and slid his cock up to rest next to her hen. Yep, it was still the softest thing to ever exist. She rolled her hips against him, eyes locked with his, reaching up to gingerly wrap her arms around his shoulders. She whispered little pleas at him, breath hot and sweat beading on her forehead.

He used his hand to guide him to her entrance. It was slick and it felt different from what he was used to. More stretchy but also not as easy to press inside of. He prodded at her entrance with his tip a few times just to hear the symphony of mewls that she made in response before finally pressing inside.

She closed her eyes and made a face. He stopped, worrying that he had hurt her or done something wrong.

“No, don’t stop. It’s nice, it’s just… it takes a second to get used to.” Her face softened a little and she let out a throaty moan as he sunk further into her. “It’s nice,” she whispered, “It’s nice it’s nice it’s nice it’s nice.” It was nice. She was warm, warmer than most women he’d ever been inside of and the heat coming off of her body so close to his own was driving him wild. She finally reopened her eyes a moment after he had sunken in as far as he could, and that gaze could have sent him over the edge right then and there.

He kissed her, and then kissed her again. He rained kisses down on her from above. Quick soft chaste kisses on the mouth and long passionate ones with just a little bit of tongue. As he pulled back all the kissing had knocked her glasses askew. She looked cute and silly and sexy like that. And that was Grelle.

He slowly started pulling out not letting himself get very far before he desperately wanted to press back in. Like that, they established a slow and intimate rhythm. He kissed at her and ran his fingers through her hair. He felt the way her breasts were pressed up against his chest and the way her legs were wrapped around him criss crossing on his back. He had never had sex like this before, it was so loving. The sex he had had with other girls was just that, sex. An activity, one that was divorced from love. What they were doing now was an expression. They were making their feelings corporeal, bringing them into the world. 

She squealed out his name every time he bottomed out in her. He had done a little research into prostate stimulation over the weekend, and while he was too nervous to try it out on himself he still angled his thrusts up to try and boop her button. She was a mess beneath him so whatever he was doing was definitely working. 

He picked up the pace a little bit, pulling out further than before before sliding right back into her. Her eyes had gone unfocused but were still staring up at him full of love. Mouth lightly slack and releasing a small trail of drool down her cheek. That combined with her still askew glasses that jiggled on her face with every thrust made him feel a pressure building deep inside him. She beat him to it.

“Cumming!” she cooed without warning as she shuddered and squeezed around him. He wasn’t quite there yet but the sight of her sweet little hen bouncing back and forth as it dribbled onto her tummy was enough to get him there. He pressed into her hips and into her as far as he could go. He kissed her deep and hard. He wrapped his entire body around hers as she did the same for him, desperately trying to make as much contact with each other's bodies as they could.

They lay there like that for a few minutes, and then a few minutes more. Grelle kissed lightly at his ear and he just drank in the feeling of her. 

“I’m glad we’re official,” she said softly into his ear. He was too, he had gone too long without loving a woman, his whole life even. He pulled out to a small whine from her, but she accepted the loss and cleaned herself up, before eagerly leading him out of the closet then down and out of the office building.

Her Accura was clean, and cozy and it smelled like her, and they listened to some of her favorite music as she drove. The roads were calm, having missed the end of rush hour traffic thanks to their little diversion.

She made good on her promise to make love to him at her apartment for the rest of the day. He even stayed the night, sleeping next to someone he loved was new to him but after a taste it wasn’t something that he would give up easily and he hoped she knew that. He knew she did.


End file.
